diff --git a/Content.Server/Chat/Systems/ChatSystem.Emote.cs b/Content.Server/Chat/Systems/ChatSystem.Emote.cs
index 8bba76dadda..bd1b944db30 100644
--- a/Content.Server/Chat/Systems/ChatSystem.Emote.cs
+++ b/Content.Server/Chat/Systems/ChatSystem.Emote.cs
@@ -1,4 +1,5 @@
 using System.Collections.Frozen;
+using System.Linq;
 using Content.Shared.Chat.Prototypes;
 using Robust.Shared.Prototypes;
 using Robust.Shared.Random;
@@ -9,6 +10,7 @@ namespace Content.Server.Chat.Systems;
 public partial class ChatSystem
 {
     private FrozenDictionary<string, EmotePrototype> _wordEmoteDict = FrozenDictionary<string, EmotePrototype>.Empty;
+    private IReadOnlyList<string> Punctuation { get; } = new List<string> { ",", ".", "!", "?", "-", "~", "'", "\"", };
 
     protected override void OnPrototypeReload(PrototypesReloadedEventArgs obj)
     {
@@ -150,6 +152,10 @@ public bool TryPlayEmoteSound(EntityUid uid, EmoteSoundsPrototype? proto, string
     private void TryEmoteChatInput(EntityUid uid, string textInput)
     {
         var actionLower = textInput.ToLower();
+        // Replace ending punctuation with nothing
+        if (Punctuation.Any(punctuation => actionLower.EndsWith(punctuation)))
+            actionLower = actionLower.Remove(actionLower.Length - 1);
+
         if (!_wordEmoteDict.TryGetValue(actionLower, out var emote))
             return;
 
diff --git a/Resources/Prototypes/DeltaV/Voice/speech_emotes.yml b/Resources/Prototypes/DeltaV/Voice/speech_emotes.yml
index 270470e702d..29f75d0d509 100644
--- a/Resources/Prototypes/DeltaV/Voice/speech_emotes.yml
+++ b/Resources/Prototypes/DeltaV/Voice/speech_emotes.yml
@@ -1,198 +1,64 @@
 - type: emote
   id: HarpyRing
   category: Vocal
-  chatMessages: [rings.]
+  chatMessages: [ rings ]
   chatTriggers:
-    - ring
-    - ring.
-    - ring!
-    - ring?
     - rings
-    - rings.
-    - rings!
-    - rings?
-    - ringing
-    - ringing.
-    - ringing!
-    - ringing?
-    - ringed
-    - ringed.
-    - ringed!
-    - ringed?
-    - rang
-    - rang.
-    - rang!
-    - rang?
 
 - type: emote
   id: HarpyPew
   category: Vocal
-  chatMessages: [pews.]
+  chatMessages: [ pews ]
   chatTriggers:
-    - pew
-    - pew.
-    - pew!
-    - pew?
     - pews
-    - pews.
-    - pews!
-    - pews?
-    - pewpew
-    - pewpew.
-    - pewpew!
-    - pewpew?
+    - pewpews
 
 - type: emote
   id: HarpyBang
   category: Vocal
-  chatMessages: [bangs.]
+  chatMessages: [ bangs ]
   chatTriggers:
-    - bang
-    - bang.
-    - bang!
-    - bang?
     - bangs
-    - bangs.
-    - bangs!
-    - bangs?
-    - banging
-    - banging.
-    - banging!
-    - banging?
-    - banged
-    - banged.
-    - banged!
-    - banged?
 
 - type: emote
   id: HarpyRev
   category: Vocal
-  chatMessages: [revs.]
+  chatMessages: [ revs ]
   chatTriggers:
-    - rev
-    - rev.
-    - rev!
-    - rev?
     - revs
-    - revs.
-    - revs!
-    - revs?
-    - revving
-    - revving.
-    - revving!
-    - revving?
-    - revved
-    - revved.
-    - revved!
-    - revved?
 
 - type: emote
   id: HarpyCaw
   category: Vocal
-  chatMessages: [caws.]
+  chatMessages: [ caws ]
   chatTriggers:
-    - caw
-    - caw.
-    - caw!
-    - caw?
     - caws
-    - caws.
-    - caws!
-    - caws?
-    - cawing
-    - cawing.
-    - cawing!
-    - cawing?
-    - cawed
-    - cawed.
-    - cawed!
-    - cawed?
 
 #Vulpkanin
 - type: emote
   id: Bark
   category: Vocal
-  chatMessages: [barks.]
+  chatMessages: [ barks ]
   chatTriggers:
-    - bark
-    - bark.
-    - bark!
-    - bark?
     - barks
-    - barks.
-    - barks!
-    - barks?
-    - barked
-    - barked.
-    - barked!
-    - barked?
-    - barking
-    - barking.
-    - barking!
-    - barking?
 
 - type: emote
   id: Snarl
   category: Vocal
-  chatMessages: [snarls.]
+  chatMessages: [ snarls ]
   chatTriggers:
-    - snarl
-    - snarl.
-    - snarl!
-    - snarl?
     - snarls
-    - snarls.
-    - snarls!
-    - snarls?
-    - snarled
-    - snarled.
-    - snarled!
-    - snarled?
-    - snarling
-    - snarling.
-    - snarling!
-    - snarling?
 
 - type: emote
   id: Whine
   category: Vocal
-  chatMessages: [whines.]
+  chatMessages: [ whines ]
   chatTriggers:
-    - whine
-    - whine.
-    - whine!
-    - whine?
     - whines
-    - whines.
-    - whines!
-    - whines?
-    - whined
-    - whined.
-    - whined!
-    - whined?
-    - whining
-    - whining.
-    - whining!
-    - whining?
 
 - type: emote
   id: Howl
   category: Vocal
-  chatMessages: [howls.]
+  chatMessages: [ howls ]
   chatTriggers:
-    - howl
-    - howl.
-    - howl!
-    - howl?
     - howls
-    - howls.
-    - howls!
-    - howls?
-    - howling
-    - howling.
-    - howling!
-    - howling?
-    - howled
-    - howled.
-    - howling!
-    - howling?
diff --git a/Resources/Prototypes/Nyanotrasen/Voice/speech_emotes.yml b/Resources/Prototypes/Nyanotrasen/Voice/speech_emotes.yml
index 697a925d896..fa471f3d705 100644
--- a/Resources/Prototypes/Nyanotrasen/Voice/speech_emotes.yml
+++ b/Resources/Prototypes/Nyanotrasen/Voice/speech_emotes.yml
@@ -2,72 +2,37 @@
 - type: emote
   id: Hiss
   category: Vocal
-  chatMessages: [hisses.]
+  chatMessages: [ hisses ]
   chatTriggers:
-    - hiss.
-    - hisses.
-    - hisses!
-    - hissing.
-    - hissed.
+    - hisses
 
 - type: emote
   id: Meow
   category: Vocal
-  chatMessages: [meows.]
+  chatMessages: [ meows ]
   chatTriggers:
-    - meow.
-    - meow!
-    - meows.
-    - meows~
-    - meows!
-    - meowing.
-    - meowed.
-    - miau.
-    - miaus.
-    - miaus!
-    - nya.
-    - nyas.
-    - nyas!
-    - mraow.
-    - mraow!
-    - mraow~
-    - mraows.
-    - mraows!
-    - mraows~
+    - meows
+    - miaus
+    - nyas
+    - mraows
 
 - type: emote
   id: Mew
   category: Vocal
-  chatMessages: [mews.]
+  chatMessages: [ mews ]
   chatTriggers:
-    - mew.
-    - mew!
-    - mew~
-    - mews.
-    - mews!
-    - mews~
-    - mewing.
-    - mewed.
+    - mews
 
 - type: emote
   id: Growl
   category: Vocal
-  chatMessages: [growls.]
+  chatMessages: [ growls ]
   chatTriggers:
-    - growl.
-    - growls.
-    - growls!
-    - growling.
-    - growled.
+    - growls
 
 - type: emote
   id: Purr
   category: Vocal
-  chatMessages: [purrs.]
+  chatMessages: [ purrs ]
   chatTriggers:
-    - purr.
-    - purrs.
-    - purrs~
-    - purrs!
-    - purring.
-    - purred.
+    - purrs
diff --git a/Resources/Prototypes/Voice/disease_emotes.yml b/Resources/Prototypes/Voice/disease_emotes.yml
index af93025cae0..7845fd3e6d2 100644
--- a/Resources/Prototypes/Voice/disease_emotes.yml
+++ b/Resources/Prototypes/Voice/disease_emotes.yml
@@ -1,45 +1,43 @@
 - type: emote
   id: Sneeze
   category: Vocal
-  chatMessages: [sneezes]
-    
+  chatMessages: [ sneezes ]
+
 - type: emote
   id: Cough
   category: Vocal
-  chatMessages: [coughs]
+  chatMessages: [ coughs ]
   chatTriggers:
-    - cough
     - coughs
 
 - type: emote
   id: CatMeow
   category: Vocal
-  chatMessages: [meows]
+  chatMessages: [ meows ]
 
 - type: emote
   id: CatHisses
   category: Vocal
-  chatMessages: [hisses]
+  chatMessages: [ hisses ]
 
 - type: emote
   id: MonkeyScreeches
   category: Vocal
-  chatMessages: [screeches]
+  chatMessages: [ screeches ]
 
 - type: emote
   id: RobotBeep
   category: Vocal
-  chatMessages: [beeps]
+  chatMessages: [ beeps ]
 
 - type: emote
   id: Yawn
   category: Vocal
-  chatMessages: [yawns]
+  chatMessages: [ yawns ]
   chatTriggers:
-    - yawn
     - yawns
 
 - type: emote
   id: Snore
   category: Vocal
-  chatMessages: [snores]
+  chatMessages: [ snores ]
diff --git a/Resources/Prototypes/Voice/speech_emotes.yml b/Resources/Prototypes/Voice/speech_emotes.yml
index 0003780099a..6c94294e2be 100644
--- a/Resources/Prototypes/Voice/speech_emotes.yml
+++ b/Resources/Prototypes/Voice/speech_emotes.yml
@@ -2,244 +2,107 @@
 - type: emote
   id: Scream
   category: Vocal
-  chatMessages: [screams!]
+  chatMessages: [ screams ]
   chatTriggers:
-    - scream
     - screams
-    - screams.
-    - screams!
-    - screaming
-    - screamed
-    - shriek
     - shrieks
-    - shrieks.
-    - shrieks!
-    - shrieking
-    - shrieked
-    - screech
     - screeches
-    - screeches.
-    - screeches!
-    - screeching
-    - screeched
-    - yell
     - yells
-    - yells.
-    - yells!
-    - yelled
-    - yelling
 
 - type: emote
   id: Laugh
   category: Vocal
-  chatMessages: [laughs]
+  chatMessages: [ laughs ]
   chatTriggers:
-    - laugh
     - laughs
-    - laughs.
-    - laughs!
-    - laughing
-    - laughed
-    - chuckle
     - chuckles
-    - chuckles.
-    - chuckles!
-    - chuckled
-    - chuckling
-    - giggle
     - giggles
-    - giggles.
-    - giggles!
-    - giggling
-    - giggled
-    - chortle
-    - chortle.
-    - chortle!
     - chortles
-    - chortles.
-    - chortles!
-    - chortling
-    - chortling.
-    - chortling!
 
 - type: emote
   id: Honk
   category: Vocal
-  chatMessages: [honks]
+  chatMessages: [ honks ]
   chatTriggers:
-    - honk
-    - honk.
-    - honk!
     - honks
-    - honks.
-    - honks!
-    - honked
-    - honked.
-    - honked!
-    - honking
-    - honking.
-    - honking!
 
 - type: emote
   id: Sigh
   category: Vocal
-  chatMessages: [sighs]
+  chatMessages: [ sighs ]
   chatTriggers:
-    - sigh
     - sighs
-    - sighed
-    - sigh.
-    - sighs.
-    - sighed.
 
 - type: emote
   id: Whistle
   category: Vocal
-  chatMessages: [whistle]
+  chatMessages: [ whistles ]
   chatTriggers:
-    - whistle
-    - whistle.
-    - whistle!
     - whistles
-    - whistles.
-    - whistles!
-    - whistleblowing
-    - whistleblowing.
-    - whistleblowing!
 
 - type: emote
   id: Crying
   category: Vocal
-  chatMessages: [crying]
+  chatMessages: [ cries ]
   chatTriggers:
-    - cry
-    - cry.
-    - cry!
-    - crying
-    - crying.
-    - crying!
     - cries
-    - cries.
-    - cries!
-    - sob
-    - sob.
     - sobs
-    - sobs.
-    - sobs!
-    - sobbing
-    - sobbing.
-    - sobbing!
 
 - type: emote
   id: Squish
   category: Vocal
-  chatMessages: [squishing]
+  chatMessages: [ squishes ]
   chatTriggers:
-    - squish
-    - squish.
-    - squish!
-    - squishing
-    - squishing.
-    - squishing!
     - squishes
-    - squishes.
-    - squishes!
 
 - type: emote
   id: Chitter
   category: Vocal
-  chatMessages: [chitters.]
+  chatMessages: [ chitters ]
   chatTriggers:
-   - chitter
-   - chitter.
-   - chitter!
    - chitters
-   - chitters.
-   - chitters!
-   - chittered
-   - chittered.
-   - chittered!
 
 - type: emote
   id: Squeak
   category: Vocal
-  chatMessages: [squeaks.]
+  chatMessages: [ squeaks ]
   chatTriggers:
-   - squeak
-   - squeak.
-   - squeak!
    - squeaks
-   - squeaks.
-   - squeaks!
-   - squeaked
-   - squeaked.
-   - squeaked!
 
 - type: emote
   id: Click
   category: Vocal
-  chatMessages: [click.]
+  chatMessages: [ clicks ]
   chatTriggers:
-   - click
-   - click.
-   - click!
-   - click?
    - clicks
-   - clicks.
-   - clicks!
-   - clicks?
-   - clicked
-   - clicked.
-   - clicked!
-   - clicked?
-   - clicking
-   - clicking.
-   - clicking!
-   - clicking?
 
 # hand emotes
 - type: emote
   id: Clap
   category: Hands
-  chatMessages: [claps!]
+  chatMessages: [ claps ]
   chatTriggers:
-    - clap
     - claps
-    - claps.
-    - claps!
-    - clapping
-    - clapped
 
 - type: emote
   id: Snap
   category: Hands
-  chatMessages: [snaps fingers] # snaps <{THEIR($ent)}> fingers?
+  chatMessages: [ snaps ] # snaps <{THEIR($ent)}> fingers?
   chatTriggers:
-    - snap
     - snaps
-    - snapping
-    - snapped
-    - snap fingers
     - snaps fingers
-    - snaps fingers.
-    - snaps fingers!
+    - snaps his fingers
+    - snaps her fingers
     - snaps their fingers
-    - snaps their fingers.
-    - snaps their fingers!
-    - snapping fingers
-    - snapped fingers
+    - snaps its fingers
+    - snaps its' fingers
 
 - type: emote
   id: Salute
   category: Hands
-  chatMessages: [Salute]
+  chatMessages: [ salutes ]
   chatTriggers:
-    - salute
-    - salute.
-    - salute!
     - salutes
-    - salutes.
-    - salutes!
 
 - type: emote
   id: DefaultDeathgasp
@@ -250,135 +113,47 @@
 - type: emote
   id: Buzz
   category: Vocal
-  chatMessages: [buzz!]
+  chatMessages: [ buzzes ]
   chatTriggers:
-    - buzzing
-    - buzzing!
-    - buzzing.
-    - buzz
-    - buzz.
-    - buzz!
-    - buzzed
-    - buzzed.
-    - buzzed!
     - buzzes
-    - buzzes.
-    - buzzes!
 
 - type: emote
   id: Weh
   category: Vocal
-  chatMessages: [Wehs!]
+  chatMessages: [ wehs ]
 
 - type: emote
   id: Chirp
   category: Vocal
-  chatMessages: [chirps!]
+  chatMessages: [ chirps ]
   chatTriggers:
-    - chirp
-    - chirp.
-    - chirp!
-    - chirp?
     - chirps
-    - chirps.
-    - chirps!
-    - chirps?
-    - chirped
-    - chirped.
-    - chirped!
-    - chirped?
-    - chirping
-    - chirping.
-    - chirping!
-    - chirping?
 
 # Machine Emotes
 - type: emote
   id: Beep
   category: Vocal
-  chatMessages: [beeps.]
+  chatMessages: [ beeps ]
   chatTriggers:
-    - beep
-    - beep!
-    - beep.
     - beeps
-    - beeps.
-    - beeps!
-    - beeped
-    - beeped.
-    - beeped!
-    - beeping
-    - beeping.
-    - beeping!
 
 - type: emote
   id: Chime
   category: Vocal
-  chatMessages: [chimes.]
+  chatMessages: [ chimes ]
   chatTriggers:
-    - chime
-    - chime.
-    - chime!
     - chimes
-    - chimes.
-    - chimes!
-    - chimed
-    - chimed.
-    - chimed!
-    - chiming
-    - chiming,
-    - chiming!
 
 - type: emote
   id: Buzz-Two
   category: Vocal
-  chatMessages: [buzzesTwice.]
+  chatMessages: [ "buzzes twice" ]
   chatTriggers:
-    - buzztwice
-    - buzztwice.
-    - buzztwice!
-    - buzzstwice
-    - buzzstwice.
-    - buzzstwice!
-    - buzzestwice
-    - buzzestwice.
-    - buzzestwice!
-    - buzzingtwice
-    - buzzingtwice.
-    - buzzingtwice!
-    - buzzedtwice
-    - buzzedtwice.
-    - buzzedtwice!
-    - buzz twice
-    - buzz twice.
-    - buzz twice!
-    - buzzs twice
-    - buzzs twice.
-    - buzzs twice!
     - buzzes twice
-    - buzzes twice.
-    - buzzes twice!
-    - buzzing twice
-    - buzzing twice.
-    - buzzing twice!
-    - buzzed twice
-    - buzzed twice.
-    - buzzed twice!
 
 - type: emote
   id: Ping
   category: Vocal
-  chatMessages: [pings.]
+  chatMessages: [ pings ]
   chatTriggers:
-    - ping
-    - ping.
-    - ping!
     - pings
-    - pings.
-    - pings!
-    - pinged
-    - pinged.
-    - pinged!
-    - pinging
-    - pinging.
-    - pinging!
diff --git a/Resources/Prototypes/Voice/tail_emotes.yml b/Resources/Prototypes/Voice/tail_emotes.yml
index 610a2ea8015..be6064b652a 100644
--- a/Resources/Prototypes/Voice/tail_emotes.yml
+++ b/Resources/Prototypes/Voice/tail_emotes.yml
@@ -2,13 +2,9 @@
   id: WagTail
   chatMessages: [wags tail]
   chatTriggers:
-    - wag
-    - wag.
-    - wags
-    - wags.
-    - wagging
-    - wagging.
-    - wag tail
-    - wag tail.
     - wags tail
-    - wags tail.
+    - wags his tail
+    - wags her tail
+    - wags their tail
+    - wags its tail
+    - wags its' tail